Identification

Summary

Fotemustine is an alkylating agent used in the treatment of metastatic melanoma.

Generic Name
Fotemustine
DrugBank Accession Number
DB04106
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 315.691
Monoisotopic: 315.075084952
Chemical Formula
C9H19ClN3O5P
Synonyms
  • (+-)-Diethyl (1-(3-(2-chloroethyl)-3-nitrosoureido)ethyl)phosphonate
  • Diethyl-1-(3-(2-chloroethyl)-3-nitrosoureido)ethylphosphonate
  • Fotemustina
  • Fotemustine
  • Fotemustinum
  • Mustoforan
External IDs
  • S 10036
  • S-10036
  • Servier-10036

Pharmacology

Indication

Not Available

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UThioredoxin reductase 1, cytoplasmicNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Darbepoetin alfaThe risk or severity of Thrombosis can be increased when Darbepoetin alfa is combined with Fotemustine.
ErythropoietinThe risk or severity of Thrombosis can be increased when Erythropoietin is combined with Fotemustine.
Methoxy polyethylene glycol-epoetin betaThe risk or severity of Thrombosis can be increased when Methoxy polyethylene glycol-epoetin beta is combined with Fotemustine.
PeginesatideThe risk or severity of Thrombosis can be increased when Peginesatide is combined with Fotemustine.
Interactions
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Food Interactions
Not Available

Products

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Categories

ATC Codes
L01AD05 — Fotemustine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dialkyl alkylphosphonates. These are compounds containing a phosphonic acid that is diesterified with alkyl groups, and the phosphorus atom is also directly attached to an alkyl group.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Organic phosphonic acids and derivatives
Sub Class
Phosphonic acid diesters
Direct Parent
Dialkyl alkylphosphonates
Alternative Parents
Phosphonic acid esters / Nitrosoureas / Semicarbazides / Nitrosamides / Organopnictogen compounds / Organophosphorus compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
show 1 more
Substituents
Aliphatic acyclic compound / Alkyl chloride / Alkyl halide / Carbonic acid derivative / Carbonyl group / Dialkyl alkylphosphonate / Hydrocarbon derivative / Nitrosamide / Nitrosourea / Organic n-nitroso compound
show 12 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
GQ7JL9P5I2
CAS number
92118-27-9
InChI Key
YAKWPXVTIGTRJH-QMMMGPOBSA-N
InChI
InChI=1S/C9H19ClN3O5P/c1-4-17-19(16,18-5-2)8(3)11-9(14)13(12-15)7-6-10/h8H,4-7H2,1-3H3,(H,11,14)/t8-/m0/s1
IUPAC Name
diethyl [(1S)-1-{[N-(2-chloroethyl)-N'-oxohydrazinecarbonyl]amino}ethyl]phosphonate
SMILES
CCOP(=O)(OCC)[C@@H](C)NC(=O)N(CCCl)N=O

References

Synthesis Reference
US4567169
General References
Not Available
PubChem Compound
46936889
PubChem Substance
46505097
ChemSpider
26330202
ChEBI
131854
ZINC
ZINC000005859934
Wikipedia
Fotemustine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentMelanoma, Malignant / Recurrent Melanoma1
3TerminatedTreatmentIntraocular Melanoma / Metastatic Cancers1
3Unknown StatusTreatmentTumors Metastatic to Brain1
2CompletedTreatmentGlioblastoma Multiforme (GBM)1
2CompletedTreatmentMalignant Melanoma of Skin1
2CompletedTreatmentMalignant Melanoma, Metastatic1
2CompletedTreatmentMelanoma, Malignant1
2CompletedTreatmentStage IV Malignant Melanoma1
2RecruitingTreatmentPrimary Central Nervous System Lymphoma (PCNSL)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Powder, for solutionIntravenous208 MG
Injection, powder, for solutionIntravenous200 mg/4ml
SolutionIntravenous
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.11 mg/mLALOGPS
logP1.23ALOGPS
logP1.28ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)11.06ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area97.3 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity71.42 m3·mol-1ChemAxon
Polarizability29.12 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9709
Blood Brain Barrier+0.7425
Caco-2 permeable-0.5823
P-glycoprotein substrateNon-substrate0.6191
P-glycoprotein inhibitor INon-inhibitor0.6195
P-glycoprotein inhibitor IINon-inhibitor0.755
Renal organic cation transporterNon-inhibitor0.8932
CYP450 2C9 substrateNon-substrate0.7887
CYP450 2D6 substrateNon-substrate0.8071
CYP450 3A4 substrateNon-substrate0.5117
CYP450 1A2 substrateNon-inhibitor0.7836
CYP450 2C9 inhibitorNon-inhibitor0.7355
CYP450 2D6 inhibitorNon-inhibitor0.8882
CYP450 2C19 inhibitorNon-inhibitor0.67
CYP450 3A4 inhibitorNon-inhibitor0.8724
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8853
Ames testAMES toxic0.9107
CarcinogenicityCarcinogens 0.7102
BiodegradationNot ready biodegradable0.8846
Rat acute toxicity3.1868 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6413
hERG inhibition (predictor II)Non-inhibitor0.8627
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Thioredoxin-disulfide reductase activity
Specific Function
Isoform 1 may possess glutaredoxin activity as well as thioredoxin reductase activity and induces actin and tubulin polymerization, leading to formation of cell membrane protrusions. Isoform 4 enha...
Gene Name
TXNRD1
Uniprot ID
Q16881
Uniprot Name
Thioredoxin reductase 1, cytoplasmic
Molecular Weight
70905.58 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 09, 2021 08:40